Chicago stand-up is the star in Michael Alexander’s new movie “Laugh Till You’re Winded”

One day back in the eighties, a young man from Chicago went to L.A. on vacation and decided to take in a show at the Comedy Store. As he waited in line, Michael Alexander had no idea that a moment was fast approaching that would change his life forever. Actually, it was a comedian who was fast approaching and his name was Carl LaBove. He was Sam Kinison’s best friend and one of the original “Outlaws of Comedy” along with Sam and Bill Hicks. Carl had noticed Michael’s stylish leather coat and couldn’t resist coming over and complimenting him. The encounter led to a backstage invite and ultimately, to Michael’s career in comedy.

Michael returned home and started getting on stage twice a week at the Comedy Cottage in Rosemont. He soon had regular gigs at Zanies, the Laugh Factory and the Improv. His ability to be spontaneously hilarious got him noticed by George Lopez one night at a post-show gathering in a Chicago bar. Not long after, he was writing for George, The Arsenio Hall Show and the Tonight Show with Jay Leno. He would open for Gladys Knight, Chicago, and Smokey Robinson.

Today he continues to make comedy history. His new movie Laugh Till You’re Winded chronicles Chicago stand-up from its first boom to its bust to its current megaton boom. The world knows Chicago for its improv, but the city’s stand-up scene is just as much an influential epicenter, producing talent on both sides of the camera and transforming American comedy and culture.

I’ve loved Chicago stand-up for many years and often dreamed of the film that would pull the one-of-a-kind story together. Now, thanks to Michael Alexander, that time is here. On Wednesday, October 24, Hannibal Buress headlines a fundraiser at Zanies in Rosemont to support the film’s completion. On Monday, November 5, Laugh Till You’re Winded will premier at Zanies in Chicago. The movie includes candid interviews with Jeff Garlin, Deon Cole, Hannibal Buress, Judy Tenuta, Tom Dreesen, Jimmy Pardo, Kyle Kinane, Lil Rel Howery, Chris Redd, Beth Stelling and more.

Michael kindly took time to speak with me by phone about his extraordinary career and how he created the film that will tell Chicago’s stand-up story to the world.


Teme: How did you know you wanted to be a comedian?

Michael: I didn’t know I wanted to be a comedian to be perfectly honest. When I got out of high school, I was a bad student and I wasn’t going to college. I had no idea what to do. So I decided to pretty much do nothing. After Carl LaBove complimented me on my coat, I hung out at the Comedy Store for the whole weekend and I got hooked. I wouldn’t be a comedian without Carl.

Michael with Carl LaBove
Michael with Carl LaBove

Teme: When was the moment you decided to get on stage?

Michael: When I was at the Comedy Store that weekend I felt jealous of the comedians. I wanted to be onstage. I wished I had already become a comedian so I could be up there performing.

Teme: What was it about comedy that spoke to you?

Michael: I liked the interaction between the audience and the comedian, and that instant response when you deliver a joke. I liked the energy of the room.

Teme: What would you say are your best memories so far of being a comedian?

Michael: My best memories were the first few years. Probably the first year in particular. The first time I was on stage at the Comedy Cottage, my ex-wife who was my girlfriend at the time was in the front row. I forgot my material and when I forgot a line, she would quote it to me.

I remember the excitement and anticipation of writing material and hoping it will go well and not knowing if it’s good or not until you get on stage. Each week I had two sets, five  minutes each, because the open mic at the Comedy Cottage was Thursday and Sunday. So all I had was ten minutes per week. Today there’s this huge open mic circuit.

Back then, stand-up comedy was more important to me than anything. It was all I thought about. I was addicted to it.


Teme: How did you go from stand-up to writing for Arsenio Hall?

Michael: During the comedy boom, I was working at a comedy club called Funny Firm on Grand and Orleans. The Improv was around the corner on Wells. I was working at one of the clubs and George Lopez and a few other comedians were working another club. We all hung out at some bar afterwards, and I was being really funny off the cuff. George said, “Hey, you’re pretty funny. You should do some writing.”

So I started to write for George. Some of the stuff he performed on television, including on the Arsenio Hall Show. I had written a joke about Denny’s. Back then, Denny’s had been denying service to blacks. My joke was, “Woke up this morning, there was a cross burning in my yard. It turns out it was just a Denny’s cooking class out on a field trip.”

I asked him if he could show Arsenio that joke, which is ridiculous, right? “Can you show this host this one single joke for me?” George said, “Hey look, I’ll try. I’m not sure if I can do that.” So George goes on [The Arsenio Hall Show] and he kills. What I wrote for him does really well. It kills. And the next morning, I was home with my five month-old daughter changing her diaper and my phone rings. It’s the producer of The Arsenio Hall Show calling on the strength of that joke and George’s recommendation. They told me they were interested in me. They had me submit stuff for about ten days and then they offered me a contract.


Teme: How did you decide to make Laugh Till You’re Winded?

Michael: I started thinking about the fact that there had never been a documentary on stand-up in Chicago. There’s one about Boston, When Stand Up Stood Out, and it’s a great documentary with Lenny Clarke, Denis Leary and Bobcat Goldthwait. There’s another one called Phunny Business [about Chicago’s legendary club All Jokes Aside].

At first, I was going to focus on the Chicago comedy boom [in the ‘80s]. Then I thought, why don’t I widen the scope and include the [current] stand-up resurgence in Chicago driven by showcases and the open mic scene?

So we talk about the pre-boom era when there were no comedy clubs. Then Tom Dreesen found a place called Le Pub, talked to the owner, and the owner agreed to allow him to do a show. He did a test show and people lined up around the building. Le Pub was the first place dedicated to stand-up comedy in Chicago.

Then Tom had a place called the Pickle Barrel over by Zanies on North Avenue and Wells. Marsha Warfield from Night Court started there. That was the first time she was on stage.

A lot of other clubs opened after that and I was lucky enough to get access to quite a few of the club owners and bookers.


Teme: Does the film cover both the clubs and the personalities?

Michael: We cover the clubs and we also highlight certain comedians. I didn’t interview Arsenio. I tried to get an interview, but I couldn’t get an interview. He’s a difficult person. But I wanted to talk about him because he’s one of the biggest people who launched out of Chicago, but he also sort of had a checkered past here.

We talk about how great a performer he was, how charismatic he was and everything else. But then there’s also a little negative. People probably thought this was going to be a love fest and celebration of stand-up comedy in Chicago. But that’s not an honest film. Stand-up comedy like anything else is a reflection of life. Certain things happen in life and that’s reflected in the film, the yin and the yang. If there’s something that’s negative, we’re not whitewashing it. We’re trying to show the positive as much as possible, but if there are people who have negative opinions … I don’t know if you saw the sizzle reel for the film?

Teme: Yes.

Michael: Deon Cole talks about having trouble getting into Zanies, and Megan Gailey and Kristen Toomey talk about sexism in stand-up. We talk about those things. For me to leave all of it out would be a disservice.

Michael with Deon Cole
Michael with Deon Cole

Teme: I wanted to ask you about that clip with Deon Cole. How could a club not book Deon Cole?

Michael: Well, the interesting thing about that is that Zanies turns 40 years old this year. They show a short film depicting its history before each show. I produced that film. I was in a meeting about it with [Zanies VP] Bert Haas at my house right before I released that sizzle reel, and I had to show it to him. He told me that he did reach out to Deon before and hopes that Deon comes to the premiere so he could meet him.

Zanies books and has booked a lot of black comedians. Zanies was twenty-five percent to a third of my work for a decade or more. One of the reasons is that I was very clean. Bert talked about it in Phunny Business and he talks about it in my film. He books his demographics.

Damon Williams is in Laugh Till You’re Winded and he even comes to Bert’s defense and says he thinks it’s more about [the demographics]. With all the clubs, there were certain types of black comedians that white clubs were more comfortable booking. Comics that were more street and more urban had trouble getting into clubs. These are facts. I know it because I lived it.

Bernie Mac was an amazing comedian. At the height of the comedy boom, there were twenty-three rooms within an hour’s radius of Chicago that were two nights or more. And do you know that I never worked with Bernie Mac? The only time that I ever saw Bernie Mac perform was at the Funny Firm. He did a guest spot once or twice, but he would come there over and over again, and they would never let him up.

Teme: I’m probably being an idiot, but why?

Michael: I don’t think it’s racism. I think it’s a need to broaden the sense of what’s funny to include people that might be different whether it be race or anything else. There’s a comedian named Paul Gilmartin. He has a fantastic podcast called The Mental Illness Happy Hour.

Paul noted that comedy clubs would never book all female shows for a regular show. They would never book all black shows. They would never have three blacks or three females on the same show. But they often have three white males. Comedians know it’s always been that way.

Eighty percent of this film is positive, but I don’t think it’s a negative to talk about things like that. It would be a boring film if all I did was show us patting ourselves on the back. It would be disingenuous. Stand-up is about life and that’s what we talk about. Real life.

Teme: What other ways has the city’s segregation shown up in the stand-up world?

Michael: There were minority acts, including women, who weren’t working who were as funny or funnier as other acts who were working. I think that with women, club owners and people expect women to talk about certain things. People stereotype female comedians thinking that, oh, they’re going to talk about feminine stuff and present a soft set. That’s not true.

The whole notion that women aren’t funny, or aren’t as funny as men is ridiculous. I oppose that question from the very beginning because it’s insulting. Funny is genderless. It has to do with your intelligence and the way that you see life.

Teme: How would you describe the state of Chicago comedy for women today?

Michael: I think it has changed. Women now are more assertive as comedians and they’re doing material that women wouldn’t have done in the past. Female comedians today are doing things that are way more real. Tougher issues, harder issues, stronger language.

I don’t think the way that other comedians or the general public perceive female comedians has changed. I think female comedians have changed themselves. The perception is still the same. I’ve heard what people say and I know what male comedians think and I know what female comedians have told me and have posted about the behavior of male comedians. So I don’t think that has changed. I think women are much more assertive and taking more control.


Teme: What is it about Chicago that launches so many notable comedians?

Michael: It was a very supportive, nurturing environment when I was coming up and it still is that way. A lot of comedians are very close to each other. Also, Chicago has many accessible open mics.

It’s all about stage time, but it’s all about being comfortable on stage and comfortable with yourself. You have to have the confidence to be able to go up there. A community where comedians are jealous and unsupportive won’t foster that.

Michael with Chris Redd
Michael with Chris Redd


Teme: Did you find common threads among the comedians you spoke with? Is there a certain personality or childhood that leads people to stand-up?

Michael: We don’t talk about that in the film, but I think it has something to do with the dark side of stand-up comedy. I’ve always thought that stand-up comics – not all, but a high percentage – are broken people. There is no doubt about it. I think a lot of comedians have had bad childhoods. They have gone through substance abuse and a lot of things. That hasn’t necessarily gotten a lot of attention.

For me, my father was very apathetic. I had physical abuse in my family growing up by my mom with me. I had a really troubled childhood and I think that has something to do with me wanting to be on stage. I think that thread of wanting to be accepted definitely runs through comedians in stand-up.

Teme: That ability to be accepted and heard …

Michael: Absolutely. We’re looking for love, acceptance. We may not be thinking consciously of that, but that is one of the key things we’re trying to get out of performing. You present the joke and you want the audience to laugh because you need them to accept that the joke is good. You need them to confirm that for you.

Teme: I’ve only done stand-up a very few times, but there was no better feeling than that.


Teme: As you were making the film, did you hear anything that surprised you?

Michael: That people had feelings about a club being racist or sexist didn’t surprise me. I know it existed before. I know that it exists now.

There were some comments about a club that closed about eight years ago. It was open over thirty years. We talk about it a lot and I interviewed the owner. This particular club was located in Oak Lawn. It was very blue collar and kind of prejudiced, to say the least. Jimmy Pardo, who is in the sizzle reel, was on Conan for years as a warm-up person and now has the podcast, Never Not Funny. He talks about the owner of that club and some things the owner said on stage. There was one particular joke that the owner said that shocked me. [Note: You have to see the movie!]


Michael: There are a lot of politics involved in making this film and in the scope of it. I’ve been in show business thirty-three years. I’ve worked for several TV shows where there is a lot of pressure if you’re a writer and especially if you’re a staff writer. This film is the most difficult thing I’ve ever done. I think I’m 5,000 hours into it right now, but it is rewarding.

Teme: It’s just sounds so good. It is the movie that needed to be made.

Michael: That’s the thing that I’ve been trying to tell everyone the entire time. This documentary, Laugh Till You’re Winded, isn’t for me. It isn’t about Michael Alexander. This film is about stand-up comedy in Chicago. This film is about the fact that we have produced people in front of the screen, but even more writers, show runners and producers and no one knows about us. It’s time that people know what an incubator Chicago is for stand-up comedy. It’s a film that should have been made a long time ago. I’m glad that I’m making it. I’m glad that it will be premiering and no matter how it turns out, it’s something special.

Michael will be on WGN Radio’s Bill and Wendy Show (10 a.m.-noon) on Monday, October 22 and on the WGN TV Morning News (6-10 a.m.) on Monday, November 5.

Hannibal Buress headlines the Laugh Till You’re Winded Fundraiser at Zanies in Rosemont on Wednesday, October 24 at 8:00 p.m. Erica Nicole Clark and Azhar Usman will also be performing. Tickets and all details here.

Laugh Till You’re Winded premiers at Zanies in Chicago on Monday, November 5 at 8:00 p.m. Tickets and all details here.

Learn more about Michael and Laugh Till You’re Winded at Thank you to Michael for allowing me to post photos from his site.

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